US12497560B2 - Organic light-emitting device and apparatus including organic light-emitting device - Google Patents

Organic light-emitting device and apparatus including organic light-emitting device

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US12497560B2
US12497560B2 US16/529,259 US201916529259A US12497560B2 US 12497560 B2 US12497560 B2 US 12497560B2 US 201916529259 A US201916529259 A US 201916529259A US 12497560 B2 US12497560 B2 US 12497560B2
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unsubstituted
aromatic condensed
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Myeongsuk KIM
Jimyoung YE
Byeongwook Yoo
Jaeho Jeong
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Samsung Display Co Ltd
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    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Definitions

  • One or more embodiments relate to an organic light-emitting device and an apparatus including the organic light-emitting device.
  • OLEDs are self-emissive devices that, as compared with other devices of the related art, have wide viewing angles, high contrast ratios, and short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed.
  • OLEDs may produce full-color images.
  • OLEDs may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region. Electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may recombine in the emission layer to produce excitons. These excitons transit (e.g., transition or relax) from an excited state to a ground state to thereby generate light.
  • One or more embodiments relate to an organic light-emitting device and an apparatus including the organic light-emitting device.
  • an organic light-emitting device may include a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the emission layer may include at least one condensed cyclic compound represented by Formula 1 and emit light in a near-infrared (NIR) region having a maximum emission wavelength of 680 nanometers (nm) or greater:
  • NIR near-infrared
  • a 1 to A 3 may each independently be selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,
  • X may be selected from B, P, and P( ⁇ O),
  • Y 1 may be selected from O, S, N(R 4 ), Si(R 4 )(R 5 ), C(R 4 )(R 5 ), and C( ⁇ O),
  • Y 2 may be selected from O, S, N(R 6 ), Si(R 6 )(R 7 ), C(R 6 )(R 7 ), and C( ⁇ O),
  • R 1 to R 3 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 60 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubsti
  • a1 to a3 may each independently be an integer from 1 to 10, wherein: when a1 is 2 or greater, at least two R 1 (s) may be identical to or different from each other; when a2 is 2 or greater, at least two R 2 (S) may be identical to or different from each other; and when a3 is 2 or greater, at least two R 3 (S) may be identical to or different from each other,
  • a 1 and A 2 may optionally be bound together via a group selected from *—O—*′, *—S—*′, *—N(R 11 )—*′, *—Si(R 11 )(R 12 )—*′, *—C(R 11 )(R 12 )—*′, *—C( ⁇ O)—*′, *—S( ⁇ O) 2 —*, *—P( ⁇ O)(R 11 )—*′ and *—P(R 11 )—*′,
  • R 4 , R 5 , R 6 , R 7 , R 11 , and R 12 may each independently be selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or
  • At least one substituent of the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
  • deuterium —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
  • Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , Q 31 to Q 33 , and Q 41 to Q 42 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl
  • * and *′ each indicate a binding site to an adjacent atom.
  • an apparatus may include the organic light-emitting device.
  • the accompanying drawing is a schematic view of an embodiment of an organic light-emitting device.
  • a layer, region, or component when referred to as being “on” or “onto” another layer, region, or component, it may be directly or indirectly formed over the other layer, region, or component. For example, intervening layers, regions, or components may be present.
  • intervening layers, regions, or components may be present.
  • an element or layer when referred to as being “between” two elements or layers, it can be the only element or layer between the two elements or layers, or one or more intervening elements or layers may also be present.
  • the expression the “(organic layer) including at least one condensed cyclic compound”, as used herein, may be construed as meaning the “(organic layer) may include a condensed cyclic compound represented by Formula 1 or at least two different condensed cyclic compounds represented by Formula 1”.
  • organic layer refers to a single layer and/or a plurality of layers between the first electrode and the second electrode in an organic light-emitting device.
  • a material included in the “organic layer” is not limited to an organic material.
  • the “organic layer” may include an inorganic material.
  • the accompanying drawing illustrates a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment.
  • the organic light-emitting device 10 may include a first electrode 110 , an organic layer 150 , and a second electrode 190 .
  • a substrate may be additionally located under the first electrode 110 or above the second electrode 190 .
  • the substrate may be a glass substrate or transparent plastic substrate, each with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
  • the first electrode 110 may be formed by depositing or sputtering, onto the substrate, a material for forming the first electrode 110 .
  • the material for forming the first electrode 110 may be selected from materials having a high work function that facilitate hole injection.
  • the first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode.
  • a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combinations thereof, but the present disclosure is not limited thereto.
  • the first electrode 110 when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, as a material for forming the first electrode 110 , at least one of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combination thereof may be used, but the present disclosure is not limited thereto.
  • the first electrode 110 may have a single-layered structure, or a multi-layered structure including two or more layers. In some embodiments, the first electrode 110 may have a triple-layered structure of ITO/Ag/ITO, but the present disclosure is not limited thereto.
  • the organic layer 150 may be on the first electrode 110 .
  • the organic layer 150 may include an emission layer.
  • the organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer.
  • the organic layer 150 may further include an electron transport region between the emission layer and the second electrode.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the organic layer may include i) a hole transport region between the first electrode and the emission layer, the hole transport region including a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and ii) an electron transport region between the emission layer and the second electrode, the electron transport region including a hole blocking layer, a buffer layer, an electron transport layer, an electron injection layer, or a combination thereof.
  • the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer, according to a sub-pixel arrangement.
  • the emission layer may have a stacked structure.
  • the stacked structure may include two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer.
  • the two or more layers may be in direct contact with each other.
  • the two or more layers may be separated from each other.
  • the emission layer may include two or more materials.
  • the two or more materials may include a red light-emitting material, a green light-emitting material, and/or a blue light-emitting material.
  • the two or more materials may be mixed with each other in a single layer.
  • the two or more materials mixed with each other in the single layer may emit white light.
  • the emission layer may include a dopant.
  • the dopant may include at least one condensed cyclic compound represented by Formula 1 that may emit near-infrared light:
  • a 1 , A 2 , A 3 , X, Y 1 , Y 2 , R 1 , R 2 , R 3 , a1, a2, and a3 may each be understood by referring to the descriptions therefor provided herein.
  • the emission layer may further include a host, and the host and the condensed cyclic compound may be included in the emission layer at a weight ratio in a range of about 95:5 to about 10:90.
  • the thickness of the emission layer may be in a range of about 100 ⁇ to about 1,000 ⁇ , and in some embodiments, about 200 ⁇ to about 600 ⁇ . When the thickness of the emission layer is within any of these ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.
  • the condensed cyclic compound may have a highest occupied molecular orbital (HOMO) energy level in a range of about 4.0 electron volts (eV) to about 6.0 eV, a lowest unoccupied molecular orbital (LUMO) energy level in a range of about 1.0 eV to about 3.0 eV, and a triplet energy (T 3 ) level of 1.5 eV or higher.
  • HOMO highest occupied molecular orbital
  • eV electron volts
  • LUMO lowest unoccupied molecular orbital
  • T 3 triplet energy
  • a 1 to A 3 may each independently be selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group.
  • At least one selected from A 1 to A 3 may be a C 1 -C 60 heterocyclic group including at least one N atom as a ring-forming atom.
  • a 1 and A 2 may each independently be a condensed polycyclic ring formed by condensation of at least two 5-membered rings, at least two 6-membered rings, or a 5-membered ring and a 6-membered ring.
  • a 1 and A 2 may be identical to or different from each other. In some embodiments, A 1 and A 2 may be identical to each other. In some embodiments, A 1 and A 2 may be different from each other.
  • a 1 and A 2 may each independently be selected from groups represented by Formulae 2-1 to 2-15, but the present disclosure is not limited thereto:
  • C 1 indicates a carbon atom bound to X in Formula 1
  • C 2 indicates a carbon atom bound to Y 1 or Y 2 in Formula 1.
  • a 3 may be a non-fused cyclic group. In some embodiments, A 3 may be a benzene group.
  • X may be B, P, or P( ⁇ O).
  • X may be B or P( ⁇ O), but the present disclosure is not limited thereto.
  • Y 1 may be selected from O, S, N(R 4 ), Si(R 4 )(R 5 ), C(R 4 )(R 5 ), and C( ⁇ O). In some embodiments, Y 1 may be selected from O, S, N(R 4 ), and Si(R 4 )(R 5 ).
  • Y 2 may be selected from O, S, N(R 6 ), Si(R 6 )(R 7 ), C(R 6 )(R 7 ), and C( ⁇ O). In some embodiments, Y 2 may be selected from O, S, N(R 6 ), and Si(R 6 )(R 7 ).
  • R 1 to R 3 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubsti
  • R 1 to R 3 may each independently be selected from:
  • a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
  • a cyclopentyl group a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group,
  • Q 1 to Q 3 and Q 31 to Q 33 may each independently be selected from:
  • R 1 to R 3 may each independently be selected from:
  • a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
  • a phenyl group a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, and a triazinyl group;
  • a1 to a3 may each independently be an integer from 1 to 10, wherein: when a1 is 2 or greater, at least two R 1 (s) may be identical to or different from each other; when a2 is 2 or greater, at least two R 2 (S) may be identical to or different from each other; and when a3 is 2 or greater, at least two R 3 (S) may be identical to or different from each other.
  • a 1 and A 2 may optionally be bound together via a group selected from *—O—*′, *—S—*′, *—N(R 11 )—*′, *—Si(R 11 )(R 12 )—*′, *—C(R 11 )(R 12 )—*′, *—C( ⁇ O)—*′, *—S( ⁇ O) 2 —*, *—P( ⁇ O)(R 11 )—*′ and *—P(R 11 )—*′.
  • R 4 , R 5 , R 6 , R 7 , R 11 , and R 12 may optionally be selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or
  • R 4 , R 5 , R 6 , R 7 , R 11 , and R 12 may each independently be selected from:
  • R 4 , R 5 , R 6 , R 7 , R 11 , and R 12 may each independently be selected from groups represented by Formulae 3-1 to 3-24, but the present disclosure is not limited thereto:
  • Y 31 may be selected from O, S, C(Z 33 )(Z 34 ), N(Z 35 ), and Si(Z 36 )(Z 37 ),
  • Z 31 to Z 37 may each independently be selected from:
  • R 4 , R 5 , R 6 , R 7 , R 11 , and R 12 may each independently be selected from groups represented by Formulae 4-1 to 4-28, but the present disclosure is not limited thereto:
  • X may be B or P( ⁇ O)
  • Y 1 may be selected from N(R 4 ), Si(R 4 )(R 5 ), and C(R 4 )(R 5 )
  • Y 2 may be selected from N(R 6 ), Si(R 6 )(R 7 ), and C(R 6 )(R 7 ).
  • R 4 and R 6 may be identical to each other, and R 5 and R 7 may be identical to each other.
  • the condensed cyclic compound represented by Formula 1 may be symmetrical with respect to an axis through X and A 3 .
  • the cyclic compound represented by Formula 1 may have C 2 or C 2v symmetry about the axis that passes through X and A 3 .
  • the condensed cyclic compound represented by Formula 1 may be selected from Compounds 1 to 126:
  • an electron donor group and an electron acceptor group may be combined, thus reducing a difference between the HOMO and LUMO energy levels of the condensed cyclic compound represented by Formula 1. Accordingly, the maximum emission wavelength of the condensed cyclic compound represented by Formula 1 may be shifted to a long wavelength region, and thus, of the condensed cyclic compound represented by Formula 1 may be configured to emit near-infrared light having a wavelength of 680 nanometers (nm) or greater.
  • the condensed cyclic compound represented by Formula 1 has an expanded ⁇ electron system, an energy level difference between the coupled orbital and the back-coupled orbital of the condensed cyclic compound represented by Formula 1 may be reduced, consequently reducing a band gap of the condensed cyclic compound represented by Formula 1.
  • an electron donor group is combined with an electron acceptor group, through charge separation, near-infrared light of which the wavelength is shifted to a longer wavelength region may be emitted by the condensed cyclic compound represented by Formula 1.
  • the hole transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
  • the hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
  • the hole transport region may have a single-layered structure including a single layer including a plurality of different materials or a multi-layered structure, e.g., a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein layers of each structure are sequentially stacked on the first electrode 110 in each stated order, but the present disclosure is not limited thereto.
  • the hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), ⁇ -NPB, TPD, a spiro-TPD, a spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4′′-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), (polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
  • L 201 to L 204 may each independently be selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
  • L 205 may be selected from *—O—*′, *—S—*′, *—N(Q 201 )-*′, a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a
  • xa1 to xa4 may each independently be an integer from 0 to 3,
  • xa5 may be an integer from 1 to 10, and
  • R 201 to R 204 and Q 201 may each independently be selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aro
  • R 201 and R 202 may optionally be bound together via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group
  • R 203 and R 204 may optionally be bound together via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
  • L 201 to L 205 may each independently be selected from:
  • Q 31 to Q 33 may each independently be selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
  • xa1 to xa4 may each independently be 0, 1, or 2.
  • xa5 may be 1, 2, 3, or 4.
  • R 201 to R 204 and Q 201 may each independently be selected from a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a
  • a phenyl group a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacen
  • At least one of R 201 to R 203 may be selected from:
  • a fluorenyl group a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
  • R 201 and R 202 may be bound together via a single bond, and/or ii) R 203 and R 204 may be bound together via a single bond.
  • At least one of R 201 to R 204 may be selected from:
  • the compound represented by Formula 201 may be represented by Formula 201A:
  • the compound represented by Formula 201 may be represented by Formula 201A(1), but the present disclosure is not limited thereto:
  • the compound represented by Formula 201 may be represented by Formula 201A-1, but the present disclosure is not limited thereto:
  • the compound represented by Formula 202 may be represented by Formula 202A:
  • the compound represented by Formula 202 may be represented by Formula 202A-1:
  • R 213 to R 217 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C 1 -C 10 alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulen
  • the hole transport region may include at least one compound selected from Compounds HT1 to HT39, but the present disclosure is not limited thereto:
  • the thickness of the hole transport region may be in a range of about 100 (Angstroms) ⁇ to about 10,000 ⁇ , and in some embodiments, about 100 ⁇ to about 1,000 ⁇ .
  • the thickness of the hole injection layer may be in a range of about 100 ⁇ to about 9,000 ⁇ , and in some embodiments, about 100 ⁇ to about 1,000 ⁇ , and the thickness of the hole transport layer may be in a range of about 50 ⁇ to about 2,000 ⁇ , and in some embodiments, about 100 ⁇ to about 1,500 ⁇ .
  • excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.
  • the emission auxiliary layer may increase light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer.
  • the electron blocking layer may reduce or eliminate the flow of electrons from an electron transport region.
  • the emission auxiliary layer and the electron blocking layer may include the aforementioned materials.
  • the lowest unoccupied molecular orbital (LUMO) of the p-dopant may be ⁇ 3.5 eV or less.
  • the p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but the present disclosure is not limited thereto.
  • the p-dopant may include at least one selected from:
  • a quinone derivative such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
  • a metal oxide such as tungsten oxide or molybdenum oxide
  • R 221 to R 223 may each independently be selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one selected from R 221 to R 223 may include at least one substituent selected from a cyano group, —F, —Cl,
  • the host may include a compound represented by Formula 301: [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 Formula 301
  • Ar 301 may be selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group,
  • xb11 may be 1, 2, or 3,
  • L 301 may be selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
  • xb1 may be an integer from 0 to 5
  • R 301 may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1
  • xb21 may be an integer from 1 to 5
  • Q 301 to Q 303 may each independently be selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the present disclosure is not limited thereto.
  • Ar 301 may be selected from:
  • a naphthalene group a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group; and
  • a naphthalene group a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group,
  • Q 31 to Q 33 may each independently be selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the present disclosure is not limited thereto.
  • the compound represented by Formula 301 may be represented by Formula 301-1 or 301-2:
  • a 301 to A 304 may each independently be selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group,
  • X 301 may be O, S, or N-[(L 304 ) xb4 -R 304 ],
  • R 311 to R 314 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C( ⁇ O)(Q 31 ), —S( ⁇ O) 2 (Q 31 ), and —P( ⁇ O)(Q 31 )(Q 32 ),
  • xb22 and xb23 may each independently be 0, 1, or 2
  • L 301 , xb1, R 301 , and Q 31 to Q 33 may each be understood by referring to the descriptions therefor provided herein,
  • L 302 to L 304 may each be understood by referring to the descriptions for L 301 provided herein,
  • xb2 to xb4 may each be understood by referring to the descriptions for xb1 provided herein, and
  • R 302 to R 304 may each be understood by referring to the descriptions for R 301 provided herein.
  • L 301 to L 304 may each independently be selected from:
  • R 301 to R 304 may each independently be selected from:
  • a phenyl group a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group,
  • a phenyl group a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group,
  • the host may include an alkaline earth metal complex.
  • the host may include a beryllium (Be) complex, e.g., Compound H55, a magnesium (Mg) complex, or a zinc (Zn) complex.
  • Be beryllium
  • Mg magnesium
  • Zn zinc
  • the host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55, but the present disclosure is not limited thereto:
  • the host may include at least one selected from a silicon-containing compound (e.g., BCPDS or the like used in Examples) and a phosphine oxide-containing compound (e.g., POPCPA or the like used in Examples).
  • a silicon-containing compound e.g., BCPDS or the like used in Examples
  • a phosphine oxide-containing compound e.g., POPCPA or the like used in Examples.
  • the host may include one type (or kind) of compounds only or two or more different types (or kinds) of compounds (for example, the constituent hosts in Examples were BCPDS and POPCPA). As such, embodiments may be modified in various ways.
  • the electron transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure each having a plurality of layers, each having a plurality of different materials.
  • the electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the present disclosure is not limited thereto.
  • the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein layers of each structure are sequentially stacked on the emission layer in each stated order, but the present disclosure is not limited thereto.
  • the electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one ⁇ electron-depleted nitrogen-containing ring.
  • Examples of the ⁇ electron-depleted nitrogen-containing ring may include an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, an indazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, a phthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline, a phenanthridine, an acridine, a phenanthroline, a phenazine, a benzimidazole, an iso-benzothiazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a tria
  • the electron transport region may include a compound represented by Formula 601: [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 Formula 601
  • Ar 601 may be selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group,
  • xe11 may be 1, 2, or 3,
  • L 601 may be selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
  • xe1 may be an integer from 0 to 5
  • R 601 may be selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
  • Q 601 to Q 603 may each independently be a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and
  • xe21 may be an integer from 1 to 5.
  • At least one selected from Ar 601 (S) in the number of xe11 and R 601 (s) in the number of xe21 may include the ⁇ electron-depleted nitrogen-containing ring.
  • ring Ar 601 may be selected from:
  • a benzene group a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group
  • a benzene group a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group
  • Q 31 to Q 33 may each independently be selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
  • Ar 601 in Formula 601 may be an anthracene group.
  • the compound represented by Formula 601 may be represented by Formula 601-1:
  • X 614 may be N or C(R 614 ), X 615 may be N or C(R 615 ), X 616 may be N or C(R 616 ), at least one selected from X 614 to X 616 may be N,
  • L 611 to L 613 may each independently be understood by referring to the descriptions for L 601 provided herein,
  • xe611 to xe613 may each independently be understood by referring to the descriptions for xe1 provided herein,
  • R 611 to R 613 may each independently be understood by referring to the descriptions for R 601 provided herein, and
  • R 614 to R 616 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
  • L 601 and L 611 to L 613 may each independently be selected from:
  • xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
  • R 601 and R 611 to R 613 may each independently be selected from:
  • a phenyl group a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group,
  • a phenyl group a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group,
  • Q 601 and Q 602 may each independently be understood by referring to the descriptions therefor provided herein.
  • the electron transport region may include at least one compound selected from Compounds ET1 to ET36, but the present disclosure is not limited thereto:
  • the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:
  • the electron transport region may include a phosphine oxide-containing compound (e.g., TSPO1 used in the Example described herein), but the present disclosure is not limited thereto.
  • the phosphine oxide-containing compound may be used in a hole blocking layer in the electron transport region, but the present disclosure is not limited thereto.
  • the thicknesses of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 ⁇ to about 1,000 ⁇ , and in some embodiments, about 30 ⁇ to about 300 ⁇ . When the thicknesses of the buffer layer, the hole blocking layer or the electron control layer are within any of these ranges, excellent hole blocking characteristics or excellent electron controlling characteristics may be obtained without a substantial increase in driving voltage.
  • the thickness of the electron transport layer may be in a range of about 100 ⁇ to about 1,000 ⁇ , and in some embodiments, about 150 ⁇ to about 500 ⁇ . When the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics may be obtained without a substantial increase in driving voltage.
  • the electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a material including metal.
  • the material including metal may include at least one selected from an alkali metal complex and an alkaline earth metal complex.
  • the alkali metal complex may include a metal ion selected from a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and a cesium (Cs) ion.
  • the alkaline earth metal complex may include a metal ion selected from a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, and a barium (Ba) ion.
  • Each ligand coordinated with the metal ion of the alkali metal complex and the alkaline earth metal complex may independently be selected from a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxydiphenyl oxadiazole, a hydroxydiphenyl thiadiazole, a hydroxyphenyl pyridine, a hydroxyphenyl benzimidazole, a hydroxyphenyl benzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but the present disclosure is not limited thereto.
  • the material including metal may include a Li complex.
  • the Li complex may include, e.g., Compound ET-D1 (lithium 8-hydroxyquinolate, LiQ) or Compound ET-D2:
  • the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190 .
  • the electron injection layer may be in direct contact with the second electrode 190 .
  • the electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers, each including a plurality of different materials.
  • the electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.
  • the alkali metal may be selected from Li, Na, K, Rb, and Cs. In an embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the present disclosure is not limited thereto.
  • the alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
  • the rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
  • the alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may each independently be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodines) of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively.
  • oxides and halides e.g., fluorides, chlorides, bromides, or iodines
  • the alkali metal compound may be selected from alkali metal oxides, such as Li 2 O, Cs 2 O, or K 2 O, and alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI.
  • the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the present disclosure is not limited thereto.
  • the alkaline earth-metal compound may be selected from alkaline earth-metal compounds, such as BaO, SrO, CaO, Ba x Sr 1-x O (wherein 0 ⁇ x ⁇ 1), and Ba x Ca 1-x O (wherein 0 ⁇ x ⁇ 1).
  • the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the present disclosure is not limited thereto.
  • the rare earth metal compound may be selected from YbF 3 , ScF 3 , ScO 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , and TbF 3 .
  • the rare earth metal compound may be selected from YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 , and TbI 3 , but the present disclosure is not limited thereto.
  • the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may each include ions of the above-described alkali metal, alkaline earth metal, and rare earth metal.
  • Each ligand coordinated with the metal ion of the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may independently be selected from a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl oxazole, a hydroxyphenyl thiazole, a hydroxydiphenyl oxadiazole, a hydroxydiphenyl thiadiazole, a hydroxyphenyl pyridine, a hydroxyphenyl benzimidazole, a hydroxyphenyl benzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but the present disclosure is
  • the electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof, as described above.
  • the electron injection layer may further include an organic material.
  • the electron injection layer further includes an organic material
  • the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or a combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
  • the thickness of the electron injection layer may be in a range of about 1 ⁇ to about 100 ⁇ , and in some embodiments, about 3 ⁇ to about 90 ⁇ . When the thickness of the electron injection layer is within any of these ranges, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.
  • the second electrode 190 may be on the organic layer 150 .
  • the second electrode 190 may be a cathode that is an electron injection electrode.
  • a material for forming the second electrode 190 may be a material having a low work function, for example, a metal, an alloy, an electrically conductive compound, or a combination thereof.
  • the second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, and IZO, but the present disclosure is not limited thereto.
  • the second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
  • the second electrode 190 may have a single-layered structure, or a multi-layered structure including two or more layers.
  • the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a set or specific region by using one or more suitable methods such as, for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser printing, and laser-induced thermal imaging.
  • suitable methods such as, for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser printing, and laser-induced thermal imaging.
  • the vacuum deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C. at a vacuum degree in a range of about 10 ⁇ 8 torr to about 10 ⁇ 3 torr, and at a deposition rate in a range of about 0.01 Angstroms per second (A/sec) to about 100 ⁇ /sec, depending on the material to be included in each layer and the structure of each layer to be formed.
  • the spin coating may be performed at a coating rate of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a heat treatment temperature of about 80° C. to about 200° C., depending on the material to be included in each layer and the structure of each layer to be formed.
  • the organic light-emitting device may be included in various suitable apparatuses.
  • the apparatus including the organic light-emitting device may be an emission apparatus, an authentication apparatus, or an electronic apparatus.
  • the emission apparatus may further include a thin film transistor (TFT) including a source electrode and a drain electrode, in addition to the organic light-emitting device described above.
  • TFT thin film transistor
  • One of the source electrode and the drain electrode of the TFT may be electrically coupled to one of a first electrode and a second electrode of the organic light-emitting device.
  • the emission apparatus may be used in various suitable displays, light sources, and/or the like.
  • the authentication apparatus may be, for example, a biometric authentication apparatus that identifies an individual according biometric information (e.g., a fingertip, a pupil, and/or the like).
  • biometric information e.g., a fingertip, a pupil, and/or the like.
  • the authentication apparatus may further include a biometric information collecting unit, in addition to the organic light-emitting device described above.
  • the electronic apparatus may be applicable to a personal computer (e.g., a mobile personal computer), a cellphone, a digital camera, an electronic note, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a blood pressure meter, a glucometer, a pulse measuring device, a pulse wave measuring device, an electrocardiograph recorder, an ultrasonic diagnosis device, an endoscope display device), a fish finder, various suitable measurement devices, gauges (e.g., gauges of an automobile, an airplane, a ship), and/or a projector, but the present disclosure is not limited thereto.
  • a personal computer e.g., a mobile personal computer
  • a cellphone e.g., a digital camera, an electronic note, an electronic dictionary, an electronic game console
  • a medical device e.g., an electronic thermometer, a blood pressure meter, a glucometer, a pulse measuring device, a pulse wave measuring device, an electrocardiograph recorder,
  • C 1 -C 60 alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.
  • C 1 -C 60 alkylene group refers to a divalent group having substantially the same structure as the C 1 -C 60 alkyl group.
  • C 2 -C 60 alkenyl group refers to a hydrocarbon group having at least one carbon-carbon double bond at a main chain (e.g., in the middle) or at a terminal end (e.g., at the terminus) of the C 2 -C 60 alkyl group. Examples thereof include an ethenyl group, a propenyl group, and a butenyl group.
  • C 2 -C 60 alkenylene group refers to a divalent group having substantially the same structure as the C 2 -C 60 alkenyl group.
  • C 2 -C 60 alkynyl group refers to a hydrocarbon group having at least one carbon-carbon triple bond at a main chain (e.g., in the middle) or at a terminal end (e.g., at the terminus) of the C 2 -C 60 alkyl group. Examples thereof include an ethynyl group and a propynyl group.
  • C 2 -C 60 alkynylene group refers to a divalent group having substantially the same structure as the C 2 -C 60 alkynyl group.
  • C 1 -C 60 alkoxy group refers to a monovalent group represented by —OA 101 (wherein A 101 is a C 1 -C 1 alkyl group). Examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
  • C 3 -C 10 cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group including 3 to 10 carbon atoms. Examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • C 3 -C 10 cycloalkylene group refers to a divalent group having substantially the same structure as the C 3 -C 10 cycloalkyl group.
  • C 1 -C 10 heterocycloalkyl group refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms. Examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group.
  • C 1 -C 10 heterocycloalkylene group refers to a divalent group having substantially the same structure as the C 1 -C 10 heterocycloalkyl group.
  • C 3 -C 10 cycloalkenyl group refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one double bond in its ring, and is not aromatic. Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.
  • C 3 -C 10 cycloalkenylene group refers to a divalent group having substantially the same structure as the C 3 -C 10 cycloalkenyl group.
  • C 1 -C 10 heterocycloalkenyl group refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring.
  • Examples of the C 1 -C 10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group.
  • C 1 -C 10 heterocycloalkylene group refers to a divalent group having substantially the same structure as the C 1 -C 10 heterocycloalkyl group.
  • C 6 -C 60 aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 6 carbon atoms.
  • C 6 -C 60 arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C 6 -C 60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group.
  • the respective rings may be fused (e.g., combined together).
  • C 1 -C 60 heteroaryl group refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 60 carbon atoms.
  • C 1 -C 60 heteroarylene group refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 60 carbon atoms.
  • Examples of the C 1 -C 60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.
  • the C 1 -C 60 heteroaryl group and the C 1 -C 60 heteroarylene group each independently include two or more rings, the respective rings may be fused (e.g., combined together).
  • C 6 -C 60 aryloxy group is represented by —OA 102 (wherein A 102 is the C 6 -C 60 aryl group).
  • C 6 -C 60 arylthio group is represented by —SA 103 (wherein A 103 is the C 6 -C 60 aryl group).
  • Examples of the monovalent non-aromatic condensed polycyclic group may include a fluorenyl group.
  • divalent non-aromatic condensed polycyclic group refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.
  • Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a carbazolyl group.
  • divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
  • C 4 -C 60 carbocyclic group refers to a monocyclic or polycyclic group having 4 to 60 carbon atoms only as ring-forming atoms.
  • the C 4 -C 60 carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group.
  • C 4 -C 60 carbocyclic group refers to a ring (e.g., a benzene group), a monovalent group (e.g., a phenyl group), or a divalent group (e.g., a phenylene group).
  • the C 4 -C 60 carbocyclic group may be a trivalent group or a quadrivalent group.
  • C 1 -C 60 heterocyclic group refers to a group having substantially the same structure as the C 4 -C 60 carbocyclic group, except that at least one heteroatom selected from N, O, Si, P, and S is used as a ring-forming atom, in addition to carbon atoms (e.g., 1 to 60 carbon atoms).
  • Ph represents a phenyl group
  • Me represents a methyl group
  • Et represents an ethyl group
  • ter-Bu represents an ethyl group
  • Bu t represents a tert-butyl group
  • OMe represents a methoxy group
  • terphenyl group refers to a phenyl group substituted with at least one phenyl group.
  • the “terphenyl group” belongs to “a substituted phenyl group” having a “C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group” as a substituent.

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Abstract

Provided are an organic light-emitting device including a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the emission layer may include at least one condensed cyclic compound represented by Formula 1 and emit light in a near-infrared (NIR) region having a maximum emission wavelength of 680 nanometers (nm) or greater:

Description

CROSS-REFERENCE TO RELATED APPLICATION
This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0114359, filed on Sep. 21, 2018, in the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference.
BACKGROUND 1. Field
One or more embodiments relate to an organic light-emitting device and an apparatus including the organic light-emitting device.
2. Description of the Related Art
Organic light-emitting devices (OLEDs) are self-emissive devices that, as compared with other devices of the related art, have wide viewing angles, high contrast ratios, and short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed. In addition, OLEDs may produce full-color images.
OLEDs may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region. Electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may recombine in the emission layer to produce excitons. These excitons transit (e.g., transition or relax) from an excited state to a ground state to thereby generate light.
SUMMARY
One or more embodiments relate to an organic light-emitting device and an apparatus including the organic light-emitting device.
Additional aspects of embodiments will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.
According to an aspect of an embodiment, an organic light-emitting device may include a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the emission layer may include at least one condensed cyclic compound represented by Formula 1 and emit light in a near-infrared (NIR) region having a maximum emission wavelength of 680 nanometers (nm) or greater:
Figure US12497560-20251216-C00002
wherein, in Formula 1,
A1 to A3 may each independently be selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
X may be selected from B, P, and P(═O),
Y1 may be selected from O, S, N(R4), Si(R4)(R5), C(R4)(R5), and C(═O),
Y2 may be selected from O, S, N(R6), Si(R6)(R7), C(R6)(R7), and C(═O),
R1 to R3 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C60 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
two groups selected from R1 to R3 that may be adjacent to each other may optionally be bound together to form a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
a1 to a3 may each independently be an integer from 1 to 10, wherein: when a1 is 2 or greater, at least two R1(s) may be identical to or different from each other; when a2 is 2 or greater, at least two R2(S) may be identical to or different from each other; and when a3 is 2 or greater, at least two R3(S) may be identical to or different from each other,
A1 and A2 may optionally be bound together via a group selected from *—O—*′, *—S—*′, *—N(R11)—*′, *—Si(R11)(R12)—*′, *—C(R11)(R12)—*′, *—C(═O)—*′, *—S(═O)2—*, *—P(═O)(R11)—*′ and *—P(R11)—*′,
R4, R5, R6, R7, R11, and R12 may each independently be selected from a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
at least one substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, Q31 to Q33, and Q41 to Q42 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* and *′ each indicate a binding site to an adjacent atom.
According to an aspect of an embodiment, an apparatus may include the organic light-emitting device.
BRIEF DESCRIPTION OF THE DRAWING
These and/or other aspects of embodiments will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawing in which:
The accompanying drawing is a schematic view of an embodiment of an organic light-emitting device.
DETAILED DESCRIPTION
Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawing, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the accompanying drawing, to explain aspects of embodiments the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
As the present disclosure allows for various changes and numerous embodiments, certain embodiments will be illustrated in the accompanying drawing and described in more detail in the written description. Effects, features, and a method of achieving embodiments of the present disclosure will be apparent to those of ordinary skill in the art when referring to the disclosed embodiments of the present disclosure with reference to the accompanying drawing. The subject matter of the present disclosure may, however, be embodied in many different forms and should not be construed as being limited to the embodiments set forth herein.
Hereinafter, the subject matter of the present disclosure will be described in more detail with reference to example embodiments of the present disclosure with reference to the accompanying drawing.
In the embodiments described in the present specification, an expression used in the singular encompasses the expression of the plural, unless it has a clearly different meaning in the context.
In the present specification, it is to be understood that the terms such as “including,” “having,” and “comprising” are intended to indicate the existence of the features or components disclosed in the specification, and are not intended to preclude the possibility that one or more other features or components may exist or may be added.
It will be understood that when a layer, region, or component is referred to as being “on” or “onto” another layer, region, or component, it may be directly or indirectly formed over the other layer, region, or component. For example, intervening layers, regions, or components may be present. In addition, it will also be understood that when an element or layer is referred to as being “between” two elements or layers, it can be the only element or layer between the two elements or layers, or one or more intervening elements or layers may also be present.
Sizes of components in the accompanying drawing may be exaggerated for convenience of explanation. In other words, because sizes and thicknesses of components in the accompanying drawing may be arbitrarily illustrated for convenience of explanation, the following embodiments are not limited thereto.
The expression the “(organic layer) including at least one condensed cyclic compound”, as used herein, may be construed as meaning the “(organic layer) may include a condensed cyclic compound represented by Formula 1 or at least two different condensed cyclic compounds represented by Formula 1”.
The term “organic layer” as used herein refers to a single layer and/or a plurality of layers between the first electrode and the second electrode in an organic light-emitting device. A material included in the “organic layer” is not limited to an organic material. For example, the “organic layer” may include an inorganic material.
The accompanying drawing illustrates a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 may include a first electrode 110, an organic layer 150, and a second electrode 190.
Hereinafter, a structure of an organic light-emitting device according to one or more embodiments and a method of manufacturing the organic light-emitting device will be described with reference to the accompanying drawing.
First Electrode 110
In the accompanying drawing, a substrate may be additionally located under the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or transparent plastic substrate, each with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
The first electrode 110 may be formed by depositing or sputtering, onto the substrate, a material for forming the first electrode 110. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function that facilitate hole injection.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combinations thereof, but the present disclosure is not limited thereto. In some embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, as a material for forming the first electrode 110, at least one of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combination thereof may be used, but the present disclosure is not limited thereto.
The first electrode 110 may have a single-layered structure, or a multi-layered structure including two or more layers. In some embodiments, the first electrode 110 may have a triple-layered structure of ITO/Ag/ITO, but the present disclosure is not limited thereto.
Organic Layer 150
The organic layer 150 may be on the first electrode 110. The organic layer 150 may include an emission layer.
The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer. The organic layer 150 may further include an electron transport region between the emission layer and the second electrode.
According to one or more embodiments, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may include i) a hole transport region between the first electrode and the emission layer, the hole transport region including a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and ii) an electron transport region between the emission layer and the second electrode, the electron transport region including a hole blocking layer, a buffer layer, an electron transport layer, an electron injection layer, or a combination thereof.
Emission Layer in Organic Layer 150
When the organic light-emitting device 10 is a full color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer, according to a sub-pixel arrangement. In one or more embodiments, the emission layer may have a stacked structure. The stacked structure may include two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer. The two or more layers may be in direct contact with each other. In some embodiments, the two or more layers may be separated from each other. In one or more embodiments, the emission layer may include two or more materials. The two or more materials may include a red light-emitting material, a green light-emitting material, and/or a blue light-emitting material. The two or more materials may be mixed with each other in a single layer. The two or more materials mixed with each other in the single layer may emit white light.
The emission layer may include a dopant. The dopant may include at least one condensed cyclic compound represented by Formula 1 that may emit near-infrared light:
Figure US12497560-20251216-C00003
wherein, in Formula 1, A1, A2, A3, X, Y1, Y2, R1, R2, R3, a1, a2, and a3 may each be understood by referring to the descriptions therefor provided herein.
The emission layer may further include a host, and the host and the condensed cyclic compound may be included in the emission layer at a weight ratio in a range of about 95:5 to about 10:90.
The thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 200 Å to about 600 Å. When the thickness of the emission layer is within any of these ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.
The condensed cyclic compound may have a highest occupied molecular orbital (HOMO) energy level in a range of about 4.0 electron volts (eV) to about 6.0 eV, a lowest unoccupied molecular orbital (LUMO) energy level in a range of about 1.0 eV to about 3.0 eV, and a triplet energy (T3) level of 1.5 eV or higher. The condensed cyclic compound has the foregoing energy levels such that the condensed cyclic compound is configured to emit near-infrared light.
In Formula 1, A1 to A3 may each independently be selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group.
In an embodiment, at least one selected from A1 to A3 may be a C1-C60 heterocyclic group including at least one N atom as a ring-forming atom.
In one or more embodiments, A1 to A3 may each independently be selected from:
a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentacene group, a pyrrole group, a cycloheptapyrrole group, a thiophene group, a thienothiophene group, a furan group, a silole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indole group, an isoindole group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a benzoquinoxaline group, a benzoquinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzothiazole group, an iso-benzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a dibenzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an oxazolopyridine group, a thiazolopyridine group, a benzonaphthyridine group, an azafluorene group, an azaspiro-bifluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an indenopyrrole group, an indolopyrrole group, an indenocarbazole group, and an indolocarbazole group.
In some embodiments, A1 to A3 may each independently be selected from a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a pyrene group, a chrysene group, a thiophene group, a furan group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a benzoquinoxaline group, a cinnoline group, a thienothiophene group, a phenanthridine group, an acridine group, a phenazine group, a benzofuran group, a benzothiophene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a dibenzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a dinaphthofuran group, a dinaphthothiophene group, an azacarbazole group, an azadibenzofuran group, and an azadibenzothiophene group, but the present disclosure is not limited thereto.
In an embodiment, A1 and A2 may each independently be a condensed polycyclic ring formed by condensation of at least two rings.
In some embodiments, A1 and A2 may each independently be a condensed polycyclic ring formed by condensation of at least two 5-membered rings, at least two 6-membered rings, or a 5-membered ring and a 6-membered ring.
In an embodiment, A1 and A2 may be identical to or different from each other. In some embodiments, A1 and A2 may be identical to each other. In some embodiments, A1 and A2 may be different from each other.
In an embodiment, A1 and A2 may each independently be selected from groups represented by Formulae 2-1 to 2-15, but the present disclosure is not limited thereto:
Figure US12497560-20251216-C00004
Figure US12497560-20251216-C00005
wherein, in Formulae 2-1 to 2-15,
C1 indicates a carbon atom bound to X in Formula 1, and
C2 indicates a carbon atom bound to Y1 or Y2 in Formula 1.
In an embodiment, A3 may be a non-fused cyclic group. In some embodiments, A3 may be a benzene group.
In Formula 1, X may be B, P, or P(═O).
In an embodiment, X may be B or P(═O), but the present disclosure is not limited thereto.
In Formula 1, Y1 may be selected from O, S, N(R4), Si(R4)(R5), C(R4)(R5), and C(═O). In some embodiments, Y1 may be selected from O, S, N(R4), and Si(R4)(R5).
In Formula 2, Y2 may be selected from O, S, N(R6), Si(R6)(R7), C(R6)(R7), and C(═O). In some embodiments, Y2 may be selected from O, S, N(R6), and Si(R6)(R7).
In Formula 1, R1 to R3 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2), wherein two groups selected from R1 to R3 that may be adjacent to each other may optionally be bound together to form a C5-C60 carbocyclic group or a C1-C60 heterocyclic group.
In an embodiment, R1 to R3 may each independently be selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group;
a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31) and —P(═O)(Q31)(Q32); and
—Si(Q1)(Q2)(Q3), —N(Q1(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
wherein Q1 to Q3 and Q31 to Q33 may each independently be selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C20 aryl group, a C1-C20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
In some embodiments, R1 to R3 may each independently be selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, and a triazinyl group.
In Formula 1, a1 to a3 may each independently be an integer from 1 to 10, wherein: when a1 is 2 or greater, at least two R1(s) may be identical to or different from each other; when a2 is 2 or greater, at least two R2(S) may be identical to or different from each other; and when a3 is 2 or greater, at least two R3(S) may be identical to or different from each other.
In Formula 1, A1 and A2 may optionally be bound together via a group selected from *—O—*′, *—S—*′, *—N(R11)—*′, *—Si(R11)(R12)—*′, *—C(R11)(R12)—*′, *—C(═O)—*′, *—S(═O)2—*, *—P(═O)(R11)—*′ and *—P(R11)—*′.
R4, R5, R6, R7, R11, and R12 may optionally be selected from a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
In an embodiment, R4, R5, R6, R7, R11, and R12 may each independently be selected from:
    • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group;
    • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group,
    • a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31) (Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
    • wherein Q31 to Q33 may each independently be selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group; and
    • a phenyl group substituted with at least one selected from —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group.
In one or more embodiments, in Formula 1, R4, R5, R6, R7, R11, and R12 may each independently be selected from groups represented by Formulae 3-1 to 3-24, but the present disclosure is not limited thereto:
Figure US12497560-20251216-C00006
Figure US12497560-20251216-C00007
Figure US12497560-20251216-C00008
Figure US12497560-20251216-C00009
wherein, in Formulae 3-1 to 3-24,
Y31 may be selected from O, S, C(Z33)(Z34), N(Z35), and Si(Z36)(Z37),
Z31 to Z37 may each independently be selected from:
    • hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group,
    • e3 may be an integer from 0 to 3,
    • e4 may be an integer from 0 to 4,
    • e5 may be an integer from 0 to 5,
    • e6 may be an integer from 0 to 6,
    • e7 may be an integer from 0 to 7,
    • e9 may be an integer from 0 to 9, and
    • indicates a binding site to an adjacent atom.
In one or more embodiments, in Formula 1, R4, R5, R6, R7, R11, and R12 may each independently be selected from groups represented by Formulae 4-1 to 4-28, but the present disclosure is not limited thereto:
Figure US12497560-20251216-C00010
Figure US12497560-20251216-C00011
Figure US12497560-20251216-C00012
Figure US12497560-20251216-C00013
In an embodiment, in Formula 1, X may be B or P(═O), Y1 may be selected from N(R4), Si(R4)(R5), and C(R4)(R5), and Y2 may be selected from N(R6), Si(R6)(R7), and C(R6)(R7).
In an embodiment, in Y1 and Y2, R4 and R6 may be identical to each other, and R5 and R7 may be identical to each other.
In an embodiment, the condensed cyclic compound represented by Formula 1 may be symmetrical with respect to an axis through X and A3. For example, the cyclic compound represented by Formula 1 may have C2 or C2v symmetry about the axis that passes through X and A3.
The condensed cyclic compound represented by Formula 1 may be selected from Compounds 1 to 126:
Figure US12497560-20251216-C00014
Figure US12497560-20251216-C00015
Figure US12497560-20251216-C00016
Figure US12497560-20251216-C00017
Figure US12497560-20251216-C00018
Figure US12497560-20251216-C00019
Figure US12497560-20251216-C00020
Figure US12497560-20251216-C00021
Figure US12497560-20251216-C00022
Figure US12497560-20251216-C00023
Figure US12497560-20251216-C00024
Figure US12497560-20251216-C00025
Figure US12497560-20251216-C00026
Figure US12497560-20251216-C00027
Figure US12497560-20251216-C00028
Figure US12497560-20251216-C00029
Figure US12497560-20251216-C00030
Figure US12497560-20251216-C00031
Figure US12497560-20251216-C00032
Figure US12497560-20251216-C00033
Figure US12497560-20251216-C00034
Figure US12497560-20251216-C00035
Figure US12497560-20251216-C00036
Figure US12497560-20251216-C00037
Figure US12497560-20251216-C00038
Figure US12497560-20251216-C00039
Figure US12497560-20251216-C00040
Figure US12497560-20251216-C00041
Figure US12497560-20251216-C00042
Figure US12497560-20251216-C00043
Figure US12497560-20251216-C00044
Figure US12497560-20251216-C00045
Figure US12497560-20251216-C00046
Figure US12497560-20251216-C00047
Figure US12497560-20251216-C00048
In the condensed cyclic compound represented by Formula 1 according to one or more embodiments, an electron donor group and an electron acceptor group may be combined, thus reducing a difference between the HOMO and LUMO energy levels of the condensed cyclic compound represented by Formula 1. Accordingly, the maximum emission wavelength of the condensed cyclic compound represented by Formula 1 may be shifted to a long wavelength region, and thus, of the condensed cyclic compound represented by Formula 1 may be configured to emit near-infrared light having a wavelength of 680 nanometers (nm) or greater.
As the condensed cyclic compound represented by Formula 1 has an expanded π electron system, an energy level difference between the coupled orbital and the back-coupled orbital of the condensed cyclic compound represented by Formula 1 may be reduced, consequently reducing a band gap of the condensed cyclic compound represented by Formula 1. When an electron donor group is combined with an electron acceptor group, through charge separation, near-infrared light of which the wavelength is shifted to a longer wavelength region may be emitted by the condensed cyclic compound represented by Formula 1.
Hole Transport Region in Organic Layer 150
The hole transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
For example, the hole transport region may have a single-layered structure including a single layer including a plurality of different materials or a multi-layered structure, e.g., a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein layers of each structure are sequentially stacked on the first electrode 110 in each stated order, but the present disclosure is not limited thereto.
The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, a spiro-TPD, a spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), (polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
Figure US12497560-20251216-C00049
Figure US12497560-20251216-C00050
Figure US12497560-20251216-C00051
wherein, in Formulae 201 and 202,
L201 to L204 may each independently be selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
L205 may be selected from *—O—*′, *—S—*′, *—N(Q201)-*′, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C2-C20 alkenylene group, a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xa1 to xa4 may each independently be an integer from 0 to 3,
xa5 may be an integer from 1 to 10, and
R201 to R204 and Q201 may each independently be selected from a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
In some embodiments, in Formula 202, R201 and R202 may optionally be bound together via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R203 and R204 may optionally be bound together via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
In an embodiment, in Formulae 201 and 202, L201 to L205 may each independently be selected from:
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group; and
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q31)(Q32)(Q33), and —N(Q31)(Q32),
wherein Q31 to Q33 may each independently be selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
In one or more embodiments, xa1 to xa4 may each independently be 0, 1, or 2.
In one or more embodiments, xa5 may be 1, 2, 3, or 4.
In one or more embodiments, R201 to R204 and Q201 may each independently be selected from a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q31)(Q32)(Q33), and —N(Q31)(Q32),
wherein Q31 to Q33 may each be understood by referring to the descriptions therefor provided herein.
In one or more embodiments, in Formula 201, at least one of R201 to R203 may be selected from:
a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, but the present disclosure is not limited thereto.
In one or more embodiments, in Formula 202, i) R201 and R202 may be bound together via a single bond, and/or ii) R203 and R204 may be bound together via a single bond.
In one or more embodiments, in Formula 202, at least one of R201 to R204 may be selected from:
a carbazolyl group; and
a carbazolyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, but the present disclosure is not limited thereto.
The compound represented by Formula 201 may be represented by Formula 201A:
Figure US12497560-20251216-C00052
In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A(1), but the present disclosure is not limited thereto:
Figure US12497560-20251216-C00053
In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1, but the present disclosure is not limited thereto:
Figure US12497560-20251216-C00054
In some embodiments, the compound represented by Formula 202 may be represented by Formula 202A:
Figure US12497560-20251216-C00055
In some embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:
Figure US12497560-20251216-C00056
In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1, L201 to L203, xa1 to xa3, xa5, and R202 to R204 may each be understood by referring to the descriptions therefor provided herein,
R211 and R212 may each be understood by referring to the descriptions for R203 provided herein, and
R213 to R217 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.
The hole transport region may include at least one compound selected from Compounds HT1 to HT39, but the present disclosure is not limited thereto:
Figure US12497560-20251216-C00057
Figure US12497560-20251216-C00058
Figure US12497560-20251216-C00059
Figure US12497560-20251216-C00060
Figure US12497560-20251216-C00061
Figure US12497560-20251216-C00062
Figure US12497560-20251216-C00063
Figure US12497560-20251216-C00064
The thickness of the hole transport region may be in a range of about 100 (Angstroms) Å to about 10,000 Å, and in some embodiments, about 100 Å to about 1,000 Å. When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and in some embodiments, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and in some embodiments, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer. The electron blocking layer may reduce or eliminate the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may include the aforementioned materials.
p-Dopant
The hole transport region may include a charge generating material as well as the aforementioned materials, to improve conductive properties of the hole transport region. The charge generating material may be substantially homogeneously or non-homogeneously dispersed in the hole transport region.
The charge generating material may include, for example, a p-dopant.
In some embodiments, the lowest unoccupied molecular orbital (LUMO) of the p-dopant may be −3.5 eV or less.
The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but the present disclosure is not limited thereto.
In some embodiments, the p-dopant may include at least one selected from:
a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
a metal oxide, such as tungsten oxide or molybdenum oxide;
1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
a compound represented by Formula 221, but the present disclosure is not limited thereto:
Figure US12497560-20251216-C00065
wherein, in Formula 221,
R221 to R223 may each independently be selected from a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one selected from R221 to R223 may include at least one substituent selected from a cyano group, —F, —Cl, —Br, —I, a C1-C20 alkyl group substituted with —F, a C1-C20 alkyl group substituted with —Cl, a C1-C20 alkyl group substituted with —Br, and a C1-C20 alkyl group substituted with —I.
Host in Emission Layer
The host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21  Formula 301
wherein, in Formula 301,
Ar301 may be selected from a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
xb11 may be 1, 2, or 3,
L301 may be selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xb1 may be an integer from 0 to 5,
R301 may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q301)(Q302)(Q303), —N(Q301)(Q302), —B(Q301)(Q302), —C(═O)(Q301), —S(═O)2(Q301), and —P(═O)(Q301)(Q302), and
xb21 may be an integer from 1 to 5,
wherein Q301 to Q303 may each independently be selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the present disclosure is not limited thereto.
In an embodiment, in Formula 301, Ar301 may be selected from:
a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group; and
a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31) (Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q31 to Q33 may each independently be selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the present disclosure is not limited thereto.
When xb11 in Formula 301 is 2 or greater, at least two Ar301(S) may be bound together via a single bond.
In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or 301-2:
Figure US12497560-20251216-C00066
wherein, in Formulae 301-1 to 301-2,
A301 to A304 may each independently be selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonapthothiophene group, and a dinaphthothiophene group,
X301 may be O, S, or N-[(L304)xb4-R304],
R311 to R314 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
xb22 and xb23 may each independently be 0, 1, or 2,
L301, xb1, R301, and Q31 to Q33 may each be understood by referring to the descriptions therefor provided herein,
L302 to L304 may each be understood by referring to the descriptions for L301 provided herein,
xb2 to xb4 may each be understood by referring to the descriptions for xb1 provided herein, and
R302 to R304 may each be understood by referring to the descriptions for R301 provided herein.
In some embodiments, in Formulae 301, 301-1, and 301-2, L301 to L304 may each independently be selected from:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q31 to Q33 may each be understood by referring to the descriptions therefor provided herein.
In some embodiments, in Formulae 301, 301-1, and 301-2, R301 to R304 may each independently be selected from:
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q31 to Q33 may each be understood by referring to the descriptions therefor provided herein.
In some embodiments, the host may include an alkaline earth metal complex. For example, the host may include a beryllium (Be) complex, e.g., Compound H55, a magnesium (Mg) complex, or a zinc (Zn) complex.
The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55, but the present disclosure is not limited thereto:
Figure US12497560-20251216-C00067
Figure US12497560-20251216-C00068
Figure US12497560-20251216-C00069
Figure US12497560-20251216-C00070
Figure US12497560-20251216-C00071
Figure US12497560-20251216-C00072
Figure US12497560-20251216-C00073
Figure US12497560-20251216-C00074
Figure US12497560-20251216-C00075
Figure US12497560-20251216-C00076
Figure US12497560-20251216-C00077
Figure US12497560-20251216-C00078
Figure US12497560-20251216-C00079
Figure US12497560-20251216-C00080
In some embodiments, the host may include at least one selected from a silicon-containing compound (e.g., BCPDS or the like used in Examples) and a phosphine oxide-containing compound (e.g., POPCPA or the like used in Examples).
The host may include one type (or kind) of compounds only or two or more different types (or kinds) of compounds (for example, the constituent hosts in Examples were BCPDS and POPCPA). As such, embodiments may be modified in various ways.
Electron Transport Region in Organic Layer 150
The electron transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure each having a plurality of layers, each having a plurality of different materials.
The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the present disclosure is not limited thereto.
In some embodiments, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein layers of each structure are sequentially stacked on the emission layer in each stated order, but the present disclosure is not limited thereto.
The electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-depleted nitrogen-containing ring.
The term “π electron-depleted nitrogen-containing ring,” as used herein, refers to a C1-C60 heterocyclic group having at least one *—N=*′ moiety as a ring-forming moiety.
For example, the “π electron-depleted nitrogen-containing ring” may be i) a 5-membered to 7-membered heteromonocyclic group having at least one *—N=*′ moiety, ii) a heteropolycyclic group in which at least two 5-membered to 7-membered heteromonocyclic groups, each having at least one *—N=*′ moiety, are condensed, or iii) a heteropolycyclic group in which at least one of a 5-membered to 7-membered heteromonocyclic group, each having at least one *—N=*′ moiety, is condensed with (e.g., combined together with) at least one C5-C60 carbocyclic group.
Examples of the π electron-depleted nitrogen-containing ring may include an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, an indazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, a phthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline, a phenanthridine, an acridine, a phenanthroline, a phenazine, a benzimidazole, an iso-benzothiazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a thiadiazole, an imidazopyridine, an imidazopyrimidine, and an azacarbazole, but the present disclosure is not limited thereto.
In some embodiments, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21  Formula 601
wherein, in Formula 601,
Ar601 may be selected from a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
xe11 may be 1, 2, or 3,
L601 may be selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xe1 may be an integer from 0 to 5,
R601 may be selected from a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q601)(Q602)(Q603), —C(═O)(Q601), —S(═O)2(Q601), and —P(═O)(Q601) (Q602),
wherein Q601 to Q603 may each independently be a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and
xe21 may be an integer from 1 to 5.
In an embodiment, at least one selected from Ar601(S) in the number of xe11 and R601(s) in the number of xe21 may include the π electron-depleted nitrogen-containing ring.
In an embodiment, in Formula 601, ring Ar601 may be selected from:
a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an iso-benzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and
a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an iso-benzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q31 to Q33 may each independently be selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
When xe11 in Formula 601 is 2 or greater, at least two Ar601(S) may be bound together via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group.
In some embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:
Figure US12497560-20251216-C00081
wherein, in Formula 601-1,
X614 may be N or C(R614), X615 may be N or C(R615), X616 may be N or C(R616), at least one selected from X614 to X616 may be N,
L611 to L613 may each independently be understood by referring to the descriptions for L601 provided herein,
xe611 to xe613 may each independently be understood by referring to the descriptions for xe1 provided herein,
R611 to R613 may each independently be understood by referring to the descriptions for R601 provided herein, and
R614 to R616 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
In an embodiment, in Formulae 601 and 601-1, L601 and L611 to L613 may each independently be selected from:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, but the present disclosure is not limited thereto.
In one or more embodiments, in Formulae 601 and 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
In one or more embodiments, in Formulae 601 and 601-1, R601 and R611 to R613 may each independently be selected from:
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; and
—S(═O)2(Q601) and —P(═O)(Q601)(Q602),
wherein Q601 and Q602 may each independently be understood by referring to the descriptions therefor provided herein.
The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but the present disclosure is not limited thereto:
Figure US12497560-20251216-C00082
Figure US12497560-20251216-C00083
Figure US12497560-20251216-C00084
Figure US12497560-20251216-C00085
Figure US12497560-20251216-C00086
Figure US12497560-20251216-C00087
Figure US12497560-20251216-C00088
Figure US12497560-20251216-C00089
Figure US12497560-20251216-C00090
Figure US12497560-20251216-C00091
Figure US12497560-20251216-C00092
Figure US12497560-20251216-C00093
In one or more embodiments, the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:
Figure US12497560-20251216-C00094
In some embodiments, the electron transport region may include a phosphine oxide-containing compound (e.g., TSPO1 used in the Example described herein), but the present disclosure is not limited thereto. In an embodiment, the phosphine oxide-containing compound may be used in a hole blocking layer in the electron transport region, but the present disclosure is not limited thereto.
The thicknesses of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, and in some embodiments, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer or the electron control layer are within any of these ranges, excellent hole blocking characteristics or excellent electron controlling characteristics may be obtained without a substantial increase in driving voltage.
The thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a material including metal.
The material including metal may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and a cesium (Cs) ion. The alkaline earth metal complex may include a metal ion selected from a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, and a barium (Ba) ion. Each ligand coordinated with the metal ion of the alkali metal complex and the alkaline earth metal complex may independently be selected from a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxydiphenyl oxadiazole, a hydroxydiphenyl thiadiazole, a hydroxyphenyl pyridine, a hydroxyphenyl benzimidazole, a hydroxyphenyl benzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but the present disclosure is not limited thereto.
For example, the material including metal may include a Li complex. The Li complex may include, e.g., Compound ET-D1 (lithium 8-hydroxyquinolate, LiQ) or Compound ET-D2:
Figure US12497560-20251216-C00095
The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers, each including a plurality of different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.
The alkali metal may be selected from Li, Na, K, Rb, and Cs. In an embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the present disclosure is not limited thereto.
The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may each independently be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodines) of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively.
The alkali metal compound may be selected from alkali metal oxides, such as Li2O, Cs2O, or K2O, and alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In an embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the present disclosure is not limited thereto.
The alkaline earth-metal compound may be selected from alkaline earth-metal compounds, such as BaO, SrO, CaO, BaxSr1-xO (wherein 0<x<1), and BaxCa1-xO (wherein 0<x<1). In an embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the present disclosure is not limited thereto.
The rare earth metal compound may be selected from YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, and TbF3. In an embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the present disclosure is not limited thereto.
The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may each include ions of the above-described alkali metal, alkaline earth metal, and rare earth metal. Each ligand coordinated with the metal ion of the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may independently be selected from a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl oxazole, a hydroxyphenyl thiazole, a hydroxydiphenyl oxadiazole, a hydroxydiphenyl thiadiazole, a hydroxyphenyl pyridine, a hydroxyphenyl benzimidazole, a hydroxyphenyl benzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but the present disclosure is not limited thereto.
The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof, as described above. In some embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or a combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and in some embodiments, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of these ranges, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.
Second Electrode 190
The second electrode 190 may be on the organic layer 150. In an embodiment, the second electrode 190 may be a cathode that is an electron injection electrode. In this embodiment, a material for forming the second electrode 190 may be a material having a low work function, for example, a metal, an alloy, an electrically conductive compound, or a combination thereof.
The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, and IZO, but the present disclosure is not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 190 may have a single-layered structure, or a multi-layered structure including two or more layers.
The layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a set or specific region by using one or more suitable methods such as, for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser printing, and laser-induced thermal imaging.
When the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are each formed by vacuum deposition, the vacuum deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C. at a vacuum degree in a range of about 10−8 torr to about 10−3 torr, and at a deposition rate in a range of about 0.01 Angstroms per second (A/sec) to about 100 Å/sec, depending on the material to be included in each layer and the structure of each layer to be formed.
When the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are each formed by spin coating, the spin coating may be performed at a coating rate of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a heat treatment temperature of about 80° C. to about 200° C., depending on the material to be included in each layer and the structure of each layer to be formed.
Apparatus
The organic light-emitting device may be included in various suitable apparatuses. In some embodiments, the apparatus including the organic light-emitting device may be an emission apparatus, an authentication apparatus, or an electronic apparatus.
In one or more embodiments, the emission apparatus may further include a thin film transistor (TFT) including a source electrode and a drain electrode, in addition to the organic light-emitting device described above. One of the source electrode and the drain electrode of the TFT may be electrically coupled to one of a first electrode and a second electrode of the organic light-emitting device. The emission apparatus may be used in various suitable displays, light sources, and/or the like.
The authentication apparatus may be, for example, a biometric authentication apparatus that identifies an individual according biometric information (e.g., a fingertip, a pupil, and/or the like).
The authentication apparatus may further include a biometric information collecting unit, in addition to the organic light-emitting device described above.
The electronic apparatus may be applicable to a personal computer (e.g., a mobile personal computer), a cellphone, a digital camera, an electronic note, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a blood pressure meter, a glucometer, a pulse measuring device, a pulse wave measuring device, an electrocardiograph recorder, an ultrasonic diagnosis device, an endoscope display device), a fish finder, various suitable measurement devices, gauges (e.g., gauges of an automobile, an airplane, a ship), and/or a projector, but the present disclosure is not limited thereto.
General Definitions of at Least Some of the Substituents
The term “C1-C60 alkyl group,” as used herein, refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. The term “C1-C60 alkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group,” as used herein, refers to a hydrocarbon group having at least one carbon-carbon double bond at a main chain (e.g., in the middle) or at a terminal end (e.g., at the terminus) of the C2-C60 alkyl group. Examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group,” as used herein, refers to a hydrocarbon group having at least one carbon-carbon triple bond at a main chain (e.g., in the middle) or at a terminal end (e.g., at the terminus) of the C2-C60 alkyl group. Examples thereof include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group,” as used herein, refers to a divalent group having substantially the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group,” as used herein, refers to a monovalent group represented by —OA101 (wherein A101 is a C1-C1 alkyl group). Examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group,” as used herein, refers to a monovalent saturated hydrocarbon monocyclic group including 3 to 10 carbon atoms. Examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C3-C10 cycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group,” as used herein, refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms. Examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group,” as used herein, refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one double bond in its ring, and is not aromatic. Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group,” as used herein, refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C6-C60 aryl group,” as used herein, refers to a monovalent group having a carbocyclic aromatic system having 6 to 6 carbon atoms. The term “C6-C60 arylene group,” as used herein, refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each independently include two or more rings, the respective rings may be fused (e.g., combined together).
The term “C1-C60 heteroaryl group,” as used herein, refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group,” as used herein, refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each independently include two or more rings, the respective rings may be fused (e.g., combined together).
The term “C6-C60 aryloxy group,” as used herein, is represented by —OA102 (wherein A102 is the C6-C60 aryl group). The term “C6-C60 arylthio group,” as used, herein is represented by —SA103 (wherein A103 is the C6-C60 aryl group).
The term “monovalent non-aromatic condensed polycyclic group,” as used herein, refers to a monovalent group that has two or more rings condensed (e.g., combined together) and only carbon atoms as ring forming atoms (e.g., 8 to 60 carbon atoms), wherein the entire molecular structure is non-aromatic. Examples of the monovalent non-aromatic condensed polycyclic group may include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group,” as used herein, refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a monovalent group that has two or more condensed rings and at least one heteroatom selected from N, O, Si, P, and S, in addition to carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, wherein the entire molecular structure is non-aromatic. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C4-C60 carbocyclic group,” as used herein, refers to a monocyclic or polycyclic group having 4 to 60 carbon atoms only as ring-forming atoms. The C4-C60 carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The term “C4-C60 carbocyclic group,” as used herein, refers to a ring (e.g., a benzene group), a monovalent group (e.g., a phenyl group), or a divalent group (e.g., a phenylene group). Also, depending on the number of substituents connected to the C4-C60 carbocyclic group, the C4-C60 carbocyclic group may be a trivalent group or a quadrivalent group.
The term “C1-C60 heterocyclic group,” as used herein, refers to a group having substantially the same structure as the C4-C60 carbocyclic group, except that at least one heteroatom selected from N, O, Si, P, and S is used as a ring-forming atom, in addition to carbon atoms (e.g., 1 to 60 carbon atoms).
In the present specification, at least one of substituents of the substituted C4-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
    • deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
    • a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
    • a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
    • a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
    • —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
    • wherein Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group; a C1-C60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group; a C6-C60 aryl group substituted with at least one selected from deuterium, —F, and a cyano group; a biphenyl group; and a terphenyl group.
“Ph,” as used herein, represents a phenyl group, “Me,” as used herein, represents a methyl group, “Et,” as used herein, represents an ethyl group, “ter-Bu” or “But,” as used herein, represents a tert-butyl group, and “OMe,” as used herein, represents a methoxy group.
The term “biphenyl group” as used herein refers to a phenyl group substituted with at least one phenyl group. The “biphenyl group” belongs to “a substituted phenyl group” having a “C6-C60 aryl group” as a substituent.
The term “terphenyl group,” as used herein, refers to a phenyl group substituted with at least one phenyl group. The “terphenyl group” belongs to “a substituted phenyl group” having a “C6-C60 aryl group substituted with a C6-C60 aryl group” as a substituent.
The symbols * and *′, as used herein, unless defined otherwise, refer to a binding site to an adjacent atom in a corresponding formula.
Hereinafter, compounds and an organic light-emitting device according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of B used was identical (or substantially identical) to an amount of A used in terms of molar equivalents.
EXAMPLES Synthesis Example 1
Synthesis of Compound 1-C
Figure US12497560-20251216-C00096
29.3 g (100.0 mmol) of Compound 1-A, 10.3 g (45.5 mmol) of Compound 1-B, 2.5 g (2.7 mmol) of Pd2(dba)3, 1.2 g (5.5 mmol) of PtBu3 (50 percent (%) solution in toluene), 26.2 g (272.7 mmol) of NaOtBu were mixed with 1,000 milliliters (mL) of toluene under a nitrogen (N2) atmosphere, followed by stirring under reflux to allow a reaction to occur for 12 hours. At room temperature, an organic layer was separated therefrom using water and ethyl acetate, and the solvent was dried. Then, through silica gel column chromatography, 19.0 g of Compound 1-C was obtained at a yield of 60%.
MS (MALDI-TOF) m/z: 695 [M]+
Synthesis of Compound 1
Figure US12497560-20251216-C00097
0 g (27.3 mmol) of Compound 1-C was dissolved in 190 mL of tert-butylbenzene, and then the temperature was adjusted to −45° C. Under a nitrogen (N2) atmosphere, 34.1 mL (54.5 mmol) of tert-butyl lithium (1.6 molar (M) solution in hexane) was slowly added dropwise thereto. Then the temperature was raised to room temperature. The temperature was then raised to 50° C., followed by stirring under reflux for 1 hour. Next, the temperature was adjusted to −45° C. 13.7 g (54.5 mmol) of boron tribromide and 14.1 g (54.5 mmol) of N,N-diisopropyl ethylamine (NetiPr2) were sequentially added dropwise to this solution. The temperature of the reaction flask was raised to room temperature, followed by stirring under reflux for 12 hours. Once the reaction was complete, an organic layer was extracted and concentrated using H2O and ethyl acetate. Then, through silica gel column chromatography, 3.3 g of Compound 1 was obtained at a yield of 18%.
MS (MALDI-TOF) m/z: 668 [M]+
Synthesis Example 2
Synthesis of Compound 5-C
Figure US12497560-20251216-C00098
14.9 g of Compound 5-C was obtained at a yield of 47% in substantially the same manner as in Synthesis of Compound 1-C, except that 29.4 g (100 mmol) of Compound 5-A was used instead of Compound 1-A.
MS (MALDI-TOF) m/z: 697 [M]+
Synthesis of Compound 5
Figure US12497560-20251216-C00099
3.3 g of Compound 5 was obtained at a yield of 23% in substantially the same manner as in Synthesis of Compound 1, except that 14.9 g (21.4 mmol) of Compound 5-C was used instead of Compound 1-C, and 149 mL of tert-butyl benzene, 26.7 mL (42.7 mmol) of tert-butyl lithium (1.6 M solution in hexane), 10.7 g (42.7 mmol) of boron tribromide, and 11.0 g (42.7 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 670 [M]+
Synthesis Example 3
Synthesis of Compound 8-C
Figure US12497560-20251216-C00100
18.8 g of Compound 8-C was obtained at a yield of 53% in substantially the same manner as in Synthesis of Compound 1-C, except that 33.6 g (100 mmol) of Compound 8-A was used instead of Compound 1-A.
MS (MALDI-TOF) m/z: 781 [M]+
Synthesis of Compound 8
Figure US12497560-20251216-C00101
2.7 g of Compound 8 was obtained at a yield of 15% in substantially the same manner as in Synthesis of Compound 1, except that 18.8 g (24.1 mmol) of Compound 8-C was used instead of Compound 1-C, and 190 mL of tert-butyl benzene, 30.1 mL (48.2 mmol) of tert-butyl lithium (1.6 M solution in hexane), 12.1 g (48.2 mmol) of boron tribromide, and 12.5 g (48.2 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 754 [M]+
Synthesis Example 4
Synthesis of Compound 11-C
Figure US12497560-20251216-C00102
31.8 g (100.0 mmol) of Compound 11-A, 22.6 g (100.0 mmol) of Compound 1-B, 2.7 g (3.0 mmol) of Pd2(dba)3, 1.3 g (6.0 mmol) of PtBu3 (50% solution in toluene), 28.8 g (300.0 mmol) of NaOtBu were mixed with 1,500 mL of toluene under a nitrogen (N2) atmosphere, followed by stirring under reflux to allow a reaction to occur for 12 hours. At room temperature, an organic layer was separated therefrom using water and ethyl acetate, and the solvent was dried. Then, through silica gel column chromatography, 20.9 g of Compound 11-C was obtained at a yield of 45%.
MS (MALDI-TOF) m/z: 463 [M]+
Synthesis of Compound 11-D
Figure US12497560-20251216-C00103
20.9 g (45.0 mmol) of Compound 11-C, 15.1 g (45.0 mmol) of Compound 8-A, 1.2 g (1.4 mmol) of Pd2(dba)3, 0.6 g (2.7 mmol) of PtBu3 (50% solution in toluene), 13.0 g (135.0 mmol) of NaOtBu were mixed with 1,000 mL of toluene under a nitrogen (N2) atmosphere, followed by stirring under reflux to allow a reaction to occur for 12 hours. At room temperature, an organic layer was separated therefrom using water and ethyl acetate, and the solvent was dried. Then, through silica gel column chromatography, 25.4 g of Compound 11-D was obtained at a yield of 74%.
MS (MALDI-TOF) m/z: 763 [M]+
Synthesis of Compound 11
Figure US12497560-20251216-C00104
2.9 g of Compound 11 was obtained at a yield of 12% in substantially the same manner as in Synthesis of Compound 1, except that 25.4 g (33.3 mmol) of Compound 11-D was used instead of Compound 1-C, and 260 mL of tert-butyl benzene, 41.6 mL (66.6 mmol) of tert-butyl lithium (1.6 M solution in hexane), 16.7 g (66.6 mmol) of boron tribromide, and 17.2 g (66.6 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 736 [M]+
Synthesis Example 5
Synthesis of Compound 13-C
Figure US12497560-20251216-C00105
23.7 g of Compound 13-C was obtained at a yield of 64% in substantially the same manner as in Synthesis of Compound 1-C, except that 17.8 g (45.5 mmol) of Compound 13-B was used instead of Compound 1-B, and Compound 8-A was used instead of Compound 1-A.
MS (MALDI-TOF) m/z: 815 [M]+
Synthesis of Compound 13
Figure US12497560-20251216-C00106
2.6 g of Compound 13 was obtained at a yield of 12% in substantially the same manner as in Synthesis of Compound 1, except that 23.7 g (29.1 mmol) of Compound 13-C was used instead of Compound 1-C, 36.4 mL (58.2 mmol) of normal-butyl lithium (1.6 M solution in hexane) was used instead of tert-butyl lithium (1.6 M solution in hexane), and 240 mL of tert-butyl benzene, 14.6 g (58.2 mmol) of boron tribromide, and 15.0 g (58.2 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 744 [M]+
Synthesis Example 6
Synthesis of Compound 17-C
Figure US12497560-20251216-C00107
27.9 g of Compound 17-C was obtained at a yield of 58% in substantially the same manner as in Synthesis of Compound 1-C, except that 36.9 g (100 mmol) of Compound 17-A was used instead of Compound 1-A, and 21.9 g (45.5 mmol) of Compound 17-B was used instead of Compound 1-B.
MS (MALDI-TOF) m/z: 1059 [M]+
Synthesis of Compound 17
Figure US12497560-20251216-C00108
7.0 g of Compound 17 was obtained at a yield of 27% in substantially the same manner as in Synthesis of Compound 1, except that 27.9 g (26.4 mmol) of Compound 17-C was used instead of Compound 1-C, 33 mL (52.7 mmol) of normal-butyl lithium (1.6 M solution in hexane) was used instead of tert-butyl lithium (1.6 M solution in hexane), and 280 mL of tert-butyl benzene, 13.2 g (52.7 mmol) of boron tribromide, and 13.6 g (52.7 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 988 [M]+
Synthesis Example 7
Synthesis of Compound 32-C
Figure US12497560-20251216-C00109
25.8 g of Compound 32-C was obtained at a yield of 62% in substantially the same manner as in Synthesis of Compound 1-C, except that 27.9 g (100 mmol) of Compound 32-A was used instead of Compound 1-A, and 21.9 g (45.5 mmol) of Compound 17-B was used instead of Compound 1-B.
MS (MALDI-TOF) m/z: 914 [M]+
Synthesis of Compound 32
Figure US12497560-20251216-C00110
6.7 g of Compound 32 was obtained at a yield of 28% in substantially the same manner as in Synthesis of Compound 1, except that 25.8 g (28.2 mmol) of Compound 32-C was used instead of Compound 1-C, 35.2 mL (56.4 mmol) of normal-butyl lithium (1.6 M solution in hexane) was used instead of tert-butyl lithium (1.6 M solution in hexane), and 260 mL of tert-butyl benzene, 14.6 g (56.4 mmol) of boron tribromide, and 14.6 g (56.4 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 843 [M]+
Synthesis Example 8
Synthesis of Compound 40-C
Figure US12497560-20251216-C00111
14.6 g of Compound 40-C was obtained at a yield of 45% in substantially the same manner as in Synthesis of Compound 1-C, except that 30.3 g (100 mmol) of Compound 40-A was used instead of Compound 1-A.
MS (MALDI-TOF) m/z: 715 [M]+
Synthesis of Compound 40
Figure US12497560-20251216-C00112
0.7 g of Compound 40 was obtained at a yield of 5% in substantially the same manner as in Synthesis of Compound 1, except that 14.6 g (20.5 mmol) of Compound 40-C was used instead of Compound 1-C, and 150 mL of tert-butyl benzene, 25.6 mL (40.9 mmol) of tert-butyl lithium (1.6 M solution in hexane), 10.2 g (40.9 mmol) of boron tribromide, and 10.6 g (40.9 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 688 [M]+
Synthesis Example 9
Synthesis of Compound 47-C
Figure US12497560-20251216-C00113
14.7 g of Compound 47-C was obtained at a yield of 42% in substantially the same manner as in Synthesis of Compound 1-C, except that 27.1 g (100 mmol) of Compound 47-A was used instead of Compound 1-A, and 17.8 g (45.5 mmol) of Compound 13-B was used instead of Compound 1-B.
MS (MALDI-TOF) m/z: 771 [M]+
Synthesis of Compound 47
Figure US12497560-20251216-C00114
0.8 g of Compound 47 was obtained at a yield of 6% in substantially the same manner as in Synthesis of Compound 1, except that 14.7 g (19.1 mmol) of Compound 47-C was used instead of Compound 1-C, 23.9 mL (38.2 mmol) of normal-butyl lithium (1.6 M solution in hexane) was used instead of tert-butyl lithium (1.6 M solution in hexane), and 140 mL of tert-butyl benzene, 9.6 g (38.2 mmol) of boron tribromide, and 9.9 g (38.2 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 700 [M]+
Synthesis Example 10
Synthesis of Compound 49-C
Figure US12497560-20251216-C00115
29.3 g (100.0 mmol) of Compound 1-A, 22.6 g (100.0 mmol) of Compound 1-B, 2.7 g (3.0 mmol) of Pd2(dba)3, 1.3 g (6.0 mmol) of PtBu3 (50% solution in toluene), 28.8 g (300.0 mmol) of NaOtBu were mixed with 1,500 mL of toluene under a nitrogen (N2) atmosphere, followed by stirring under reflux to allow a reaction to occur for 12 hours. At room temperature, an organic layer was separated therefrom using water and ethyl acetate, and the solvent was dried. Then, through silica gel column chromatography, 28.5 g of compound 49-C was obtained at a yield of 65%.
MS (MALDI-TOF) m/z: 438 [M]+
Synthesis of Compound 49-E
Figure US12497560-20251216-C00116
28.5 g (65.0 mmol) of Compound 49-C, 17.5 g (65.0 mmol) of Compound 49-D, 1.8 g (2.0 mmol) of Pd2(dba)3, 0.9 g (3.9 mmol) of PtBu3 (50% solution in toluene), 18.7 g (195.0 mmol) of NaOtBu were mixed with 1,500 mL of toluene under a nitrogen (N2) atmosphere, followed by stirring under reflux to allow a reaction to occur for 12 hours. At room temperature, an organic layer was separated therefrom using water and ethyl acetate, and the solvent was dried. Then, through silica gel column chromatography, 30.5 g of compound 49-E was obtained at a yield of 70%.
MS (MALDI-TOF) m/z: 671 [M]+
Synthesis of Compound 49
Figure US12497560-20251216-C00117
7.3 g of Compound 49 was obtained at a yield of 25% in substantially the same manner as in Synthesis of Compound 1, except that 30.5 g (45.5 mmol) of Compound 49-E was used instead of Compound 1-C, and 310 mL of tert-butyl benzene, 56.9 mL (91.0 mmol) of tert-butyl lithium (1.6 M solution in hexane), 22.8 g (91.0 mmol) of boron tribromide, and 23.5 g (91.0 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 700 [M]+
Synthesis Example 11
Synthesis of Compound 70-C
Figure US12497560-20251216-C00118
22.1 g of Compound 70-C was obtained at a yield of 62% in substantially the same manner as in Synthesis of Compound 1-C, except that 30.9 g (100 mmol) of Compound 70-A was used instead of Compound 1-A, and 14.9 g (45.5 mmol) of Compound 70-B was used instead of Compound 1-B.
MS (MALDI-TOF) m/z: 785 [M]+
Synthesis of Compound 70
Figure US12497560-20251216-C00119
5.4 g of Compound 70 was obtained at a yield of 27% in substantially the same manner as in Synthesis of Compound 1, except that 22.1 g (28.2 mmol) of Compound 70-C was used instead of Compound 1-C, 35.2 mL (56.4 mmol) of normal-butyl lithium (1.6 M solution in hexane) was used instead of tert-butyl lithium (1.6 M solution in hexane), and 220 mL of tert-butyl benzene, 14.6 g (56.4 mmol) of boron tribromide, and 14.6 g (56.4 mmol) of N,N-diisopropyl ethylamine were used.
MS (MALDI-TOF) m/z: 714 [M]+
Synthesis Example 12
Synthesis of Compound 85-A
Figure US12497560-20251216-C00120
13.9 g (20.0 mmol) of Compound 1-C was dissolved in 100 mL of toluene, and then the temperature was adjusted to −45° C. Under a nitrogen (N2) atmosphere, 25.0 mL (40.0 mmol) of tert-butyl lithium (1.6 M solution in hexane) was slowly added dropwise thereto. Then the temperature was raised to room temperature. The temperature was then raised to 50° C., followed by stirring under reflux for 4 hours. Next, the temperature was adjusted to −45° C. 5.5 g (40 mmol) of PCl3 was added dropwise to this solution, and the temperature of the reaction flask was raised to room temperature, followed by stirring under reflux for 2 hours. Once the reaction was complete, the solvent was removed therefrom by evaporation, and a residue was dissolved in 200 mL of o-dichlorobenzene. Then, the temperature was adjusted to 0° C. 11.3 g (44.0 mmol) of S8 was added thereto, followed by raising the temperature and stirring under reflux for 12 hours. Once the reaction was complete, an organic layer was extracted and concentrated using H2O and ethyl acetate. Then, through silica gel column chromatography, 6.5 g of Compound 85-A was obtained at a yield of 45.0%.
MS (MALDI-TOF) m/z: 720 [M]+
Synthesis of Compound 85
Figure US12497560-20251216-C00121
6.5 g (9.0 mmol) of Compound 85-A was dissolved in 180 mL of dichloromethane, and then the temperature was adjusted to −30° C. 8.1 g (46.8 mmol, 77 wt %) of m-CBPA was added thereto, followed by stirring for 2 hours. Next, 180 mL of supersaturated Na2SO3 was added to this solution, and then an organic layer was separated and concentrated. The concentrated solid was subjected to a silica gel column chromatography to thereby obtain 4.8 g of Compound 85 at a yield of 75%.
MS (MALDI-TOF) m/z: 704 [M]+
Synthesis Example 13
Synthesis of Compound 109-A
Figure US12497560-20251216-C00122
5.6 g of Compound 109-A was obtained at a yield of 40% in substantially the same manner as in Synthesis of Compound 12-A, except that 13.4 g (20.0 mmol) of Compound 49-E was used instead of Compound 1-C.
MS (MALDI-TOF) m/z: 696 [M]+
Synthesis of Compound 109
Figure US12497560-20251216-C00123
5.6 g (8.0 mmol) of Compound 109-A was dissolved in 160 mL of dichloromethane, and then the temperature was adjusted to −30° C. 7.2 g (41.6 mmol, 77 wt %) of m-CBPA was added thereto, followed by stirring for 2 hours. Next, 160 mL of supersaturated Na2SO3 was added to this solution, and then an organic layer was separated and concentrated. The concentrated solid was subjected to a silica gel column chromatography to thereby obtain 3.7 g of Compound 109 at a yield of 68%.
MS (MALDI-TOF) m/z: 680 [M]+
Example 1
An anode of a glass substrate, on which ITO was formed to a thickness of 120 nm, was ultrasonically cleaned and pretreated (UV and O3 heat-treatment).
Compound HT6 and HAT-CN were co-deposited on the anode to form a hole transport layer having a thickness of 120 nm.
Compound H56, i.e., a host, and Compound 1, i.e., a dopant, were co-deposited on the hole transport layer to a weight ratio of 98:2, thereby forming an emission layer having a thickness of about 30 nm.
Next, BAlq was deposited on the emission layer to form a hole blocking layer having a thickness of 5 nm. Then, Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 25 nm. LiF was then deposited on the electron transport layer to form an electron injection layer having a thickness of 0.5 nm. Lastly, aluminum (Al) was deposited on the electron injection layer to form a cathode having a thickness of 150 nm, thereby completing the manufacture of an light-emitting device having a structure of ITO (120 nm)/HT6:HAT-CN (120 nm)/H56:1 (2 wt %, 30 nm)/Alq (25 nm)/Al (150 nm).
Examples 2 to 13
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that Compounds 5, 8, 11, 13, 17, 32, 40, 47, 49, 70, 85, and 109 were used instead of Compound 1 as a dopant.
Evaluation Example 1
The driving voltage, current density, external quantum luminous efficiency, and maximum emission wavelength of the organic light-emitting devices manufactured in Examples 1 to 13 were measured by using Keithley source-measure unit (SMU) 236 and a luminance meter PR650.
The organic light-emitting devices of Examples 1 to 13 were found to have low driving voltage and high external quantum luminous efficiency as compared to other organic light-emitting devices in the related art, while emitting, for example, near-infrared light having a maximum emission wavelength of 680 nm or greater.
As apparent from the foregoing description, the organic light-emitting device may emit light of a near-infrared (NIR) region while having a low driving voltage and high efficiency.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.
It will be understood that, although the terms “first,” “second,” “third,” etc., may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, a first element, component, region, layer or section described below could be termed a second element, component, region, layer or section, without departing from the spirit and scope of the present disclosure.
Spatially relative terms, such as “beneath,” “below,” “lower,” “under,” “above,” “upper,” and the like, may be used herein for ease of explanation to describe one element or feature's relationship to another element(s) or feature(s) as illustrated in the figures. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or in operation, in addition to the orientation depicted in the figures. For example, if the device in the figures is turned over, elements described as “below” or “beneath” or “under” other elements or features would then be oriented “above” the other elements or features. Thus, the example terms “below” and “under” can encompass both an orientation of above and below. The device may be otherwise oriented (e.g., rotated 90 degrees or at other orientations) and the spatially relative descriptors used herein should be interpreted accordingly.
As used herein, the terms “substantially,” “about,” and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. Further, the use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure.” As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively. Also, the term “exemplary” is intended to refer to an example or illustration.
Also, any numerical range recited herein is intended to include all subranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein, and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
While one or more embodiments have been described with reference to the accompanying drawing, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims, and equivalents thereof.

Claims (19)

What is claimed is:
1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer between the first electrode and the second electrode and comprising an emission layer,
wherein the emission layer comprises at least one condensed cyclic compound represented by Formula 1 and emits light in a near-infrared (NIR) region having a maximum emission wavelength of 680 nanometers (nm) or greater:
Figure US12497560-20251216-C00124
wherein, in Formula 1,
A1 and A2 are each independently selected from the group consisting of groups represented by Formulae 2-2, 2-5, 2-6, and 2-9 to 2-15:
Figure US12497560-20251216-C00125
Figure US12497560-20251216-C00126
X is selected from the group consisting of B, P, and P(═O),
wherein, when one of A1 or A2 is a group represented by Formula 2-10, the other of A1 or A2 is a group represented by Formula 2-2, 2-5, 2-6, 2-9, 2-11, 2-12, 2-13, 2-14 or 2-15, when one of A1 or A2 is a group represented by Formula 2-15 and X is B, the other of A1 or A2 is selected from the group consisting of groups represented by Formulae 2-2, 2-5, 2-6, and 2-9 to 2-14, and when one of A1 or A2 is a group represented by Formula 2-11, the other of A1 or A2 is a group represented by Formula 2-2, 2-5, 2-6, 2-9, 2-10, 2-12, 2-13, 2-14 or 2-15,
wherein, in Formulae 2-2, 2-5, 2-6, and 2-9 to 2-15,
C1 indicates a carbon atom bound to X in Formula 1, and
C2 indicates a carbon atom bound to Y1 or Y2 in Formula 1,
A3 is selected from the group consisting of a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
Y1 is selected from the group consisting of O, S, N(R4), Si(R4)(R5), C(R4)(R5), and C(═O),
Y2 is selected from the group consisting of O, S, N(R6), Si(R6)(R7), C(R6)(R7), and C(═O),
R1 to R3 are each independently selected from the group consisting of hydrogen, deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
two groups selected from R1 to R3 that are adjacent to each other are optionally bound together to form a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
a1 to a3 are each independently an integer from 1 to 10, wherein: when a1 is 2 or greater, at least two R1(s) are identical to or different from each other; when a2 is 2 or greater, at least two R2(s) are identical to or different from each other; and when a3 is 2 or greater, at least two R3(s) are identical to or different from each other,
A1 and A2 are optionally bound together via a group selected from the group consisting of *—O—*′, *—S—*′, *—N(R11)—*′, *—Si(R11)(R12)—*′, *—C(R11)(R12)—*′, *—C(═O)—*′, *—S(═O)2—*′, *—P(═O)(R11)—*′ and *—P(R11)—*′, wherein when at least one of A1 or A2 is represented by Formula 2-10 or 2-11, A1 and A2 are not bound together by *—O—*′, *—S—*′, or *—N(R11)—*′,
R4, R5, R6, R7, R11, and R12 are each independently selected from the group consisting of a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
at least one substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:
deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from the group consisting of deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from the group consisting of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, Q31 to Q33, and Q41 to Q42 are each independently selected from the group consisting of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* and *′ each indicate a binding site to an adjacent atom.
2. The organic light-emitting device of claim 1, wherein the first electrode is an anode, the second electrode is a cathode, and the organic layer comprises: i) a hole transport region between the first electrode and the emission layer, the hole transport region comprising a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and ii) an electron transport region between the emission layer and the second electrode, the electron transport region comprising a hole blocking layer, a buffer layer, an electron transport layer, an electron injection layer, or a combination thereof.
3. The organic light-emitting device of claim 1, wherein the emission layer further comprises a host, and the host and the at least one condensed cyclic compound are comprised in the emission layer at a weight ratio in a range of about 95:5 to about 10:90.
4. The organic light-emitting device of claim 1, wherein the at least one condensed cyclic compound has a highest occupied molecular orbital (HOMO) energy level in a range of about 4.0 electron volts (eV) to about 6.0 eV, a lowest unoccupied molecular orbital (LUMO) energy level in a range of about 1.0 eV to about 3.0 eV, and a triplet energy (T3) level of 1.5 eV or higher.
5. The organic light-emitting device of claim 1, wherein, in Formula 1, A3 is selected from the group consisting of:
a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentacene group, a pyrrole group, a cycloheptapyrrole group, a thiophene group, a thienothiophene group, a furan group, a silole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indole group, an isoindole group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a benzoquinoxaline group, a benzoquinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzothiazole group, an iso-benzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a dibenzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an oxazolopyridine group, a thiazolopyridine group, a benzonaphthyridine group, an azafluorene group, an azaspiro-bifluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an indenopyrrole group, an indolopyrrole group, an indenocarbazole group, and an indolocarbazole group.
6. The organic light-emitting device of claim 1, wherein, in Formula 1, A3 is selected from the group consisting of:
a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a pyrene group, a chrysene group, a thiophene group, a furan group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a benzoquinoxaline group, a cinnoline group, a thienothiophene group, a phenanthridine group, an acridine group, a phenazine group, a benzofuran group, a benzothiophene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a dibenzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a dinaphthofuran group, a dinaphthothiophene group, an azacarbazole group, an azadibenzofuran group, and an azadibenzothiophene group.
7. The organic light-emitting device of claim 1, wherein A1 and A2 are identical to each other.
8. The organic light-emitting device of claim 1, wherein A3 is a non-fused cyclic group.
9. The organic light-emitting device of claim 1, wherein R1 to R3 are each independently selected from the group consisting of:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from the group consisting of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group;
a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group, each substituted with at least one selected from the group consisting of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, —Si(Q31)(Q32) (Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31) and —P(═O)(Q31)(Q32); and
—Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
wherein Q1 to Q3 and Q31 to Q33 are each independently selected from the group consisting of:
hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C20 aryl group, a C1-C20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
10. The organic light-emitting device of claim 1, wherein R4, R5, R6, R7, R11, and R12 are each independently selected from the group consisting of:
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, and an imidazopyridinyl group, each substituted with at least one selected from the group consisting of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q31 to Q33 are each independently selected from the group consisting of a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group; and
a phenyl group substituted with at least one selected from the group consisting of —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group.
11. The organic light-emitting device of claim 1, wherein in Formula 1, R4, R5, R6, R7, R11, and R12 are each independently selected from the group consisting of groups represented by Formulae 4-1 to 4-28:
Figure US12497560-20251216-C00127
Figure US12497560-20251216-C00128
Figure US12497560-20251216-C00129
Figure US12497560-20251216-C00130
12. The organic light-emitting device of claim 1, wherein, in Formula 1, X is selected from the group consisting of B and P(═O), Y1 is selected from the group consisting of N(R4), Si(R4)(R5), and C(R4)(R5), and Y2 is selected from the group consisting of N(R6), Si(R6)(R7), and C(R6)(R7).
13. The organic light-emitting device of claim 12, wherein R4 is identical to R6, and R5 is identical to R7.
14. The organic light-emitting device of claim 1, wherein the at least one condensed cyclic compound represented by Formula 1 is symmetrical with respect to an axis through X and A3.
15. An apparatus comprising the organic light-emitting device of claim 1.
16. The apparatus of claim 15, wherein the apparatus is an emission device, an authentication device, or an electronic device.
17. The organic light-emitting device of claim 1, wherein A1 and A2 are different from each other.
18. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer between the first electrode and the second electrode and comprising an emission layer,
wherein the emission layer comprises at least one condensed cyclic compound and emits light in a near-infrared (NIR) region having a maximum emission wavelength of 680 nanometers (nm) or greater, and
wherein the at least one condensed cyclic compound represented by Formula 1 is selected from the group consisting of Compounds 33 to 36, 45 to 48, 51 to 58, 69, 71 to 78, 80, 83, 84, 101 to 113, 120 to 124, and 126:
Figure US12497560-20251216-C00131
Figure US12497560-20251216-C00132
Figure US12497560-20251216-C00133
Figure US12497560-20251216-C00134
Figure US12497560-20251216-C00135
Figure US12497560-20251216-C00136
Figure US12497560-20251216-C00137
Figure US12497560-20251216-C00138
Figure US12497560-20251216-C00139
Figure US12497560-20251216-C00140
Figure US12497560-20251216-C00141
Figure US12497560-20251216-C00142
Figure US12497560-20251216-C00143
Figure US12497560-20251216-C00144
Figure US12497560-20251216-C00145
Figure US12497560-20251216-C00146
Figure US12497560-20251216-C00147
Figure US12497560-20251216-C00148
19. A fused cyclic compound represented by Formula 1:
Figure US12497560-20251216-C00149
wherein, in Formula 1,
A1 and A2 are each independently selected from the group consisting of groups represented by Formulae 2-2, 2-5, 2-6, and 2-9 to 2-15:
Figure US12497560-20251216-C00150
X is selected from the group consisting of B, P, and P(═O),
wherein, when one of A1 or A2 is a group represented by Formula 2-10, the other of A1 or A2 is a group represented by Formula 2-2, 2-5, 2-6, 2-9, 2-11, 2-12, 2-13, 2-14 or 2-15, when one of A1 or A2 is a group represented by Formula 2-15 and X is B, the other of A1 or A2 is selected from the group consisting of groups represented by Formulae 2-2, 2-5, 2-6, and 2-9 to 2-14, and when one of A1 or A2 is a group represented by Formula 2-11, the other of A1 or A2 is a group represented by Formula 2-2, 2-5, 2-6, 2-9, 2-10, 2-12, 2-13, 2-14 or 2-15,
wherein, in Formulae 2-2, 2-5, 2-6, and 2-9 to 2-15,
C1 indicates a carbon atom bound to X in Formula 1, and
C2 indicates a carbon atom bound to Y1 or Y2 in Formula 1,
A3 is selected from the group consisting of a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
Y1 is selected from the group consisting of O, S, N(R4), Si(R4)(R5), C(R4)(R5), and C(═O),
Y2 is selected from the group consisting of O, S, N(R6), Si(R6)(R7), C(R6)(R7), and C(═O),
R1 to R3 are each independently selected from the group consisting of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
two groups selected from R1 to R3 that are adjacent to each other are optionally bound together to form a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
a1 to a3 are each independently an integer from 1 to 10; when a1 is 2 or greater, at least two R1(s) are identical to or different from each other; when a2 is 2 or greater, at least two R2(s) are identical to or different from each other; and when a3 is 2 or greater, at least two R3(s) are identical to or different from each other,
A1 and A2 are optionally bound together via a group selected from the group consisting of *—O—*′, *—S—*′, *—N(R11)—*′, *—Si(R11)(R12)—*′, *—C(R11)(R12)—*′, *′C(═O)—*′, *—S(═O)2—*′, *—P(═O)(R11)—*′ and *—P(R11)—*′, wherein when at least one of A1 or A2 is represented by Formula 2-10 or 2-11, A1 and A2 are not bound together by *—O—*′, *—S—*′, or *—N(R11)—*′,
R4, R5, R6, R7, R11, and R12 are each independently selected from the group consisting of a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
at least one substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from the group consisting of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from the group consisting of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, Q31 to Q33, and Q41 to Q42 are each independently selected from the group consisting of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* and *′ each indicate a binding site to an adjacent atom.
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